


Lesson Learned

by AnaliseGrey



Series: Along the Way Adjacent [5]
Category: Critical Role (Web Series)
Genre: Figging, Light BDSM, Light D/s, M/M, Magical restraints, Sex
Language: English
Status: Completed
Published: 2019-04-14
Updated: 2019-04-14
Packaged: 2020-01-13 02:05:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,029
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18459230
Author URL: https://archiveofourown.org/users/AnaliseGrey/pseuds/AnaliseGrey
Summary: Their travel earlier was calm and relaxed, but Molly gets bored easily, and there’s only so many ways he can practice his cards, or clean his swords, or doze in the sun in the back of the wagon with Frumpkin, and so he’d turned to his next favorite form of entertainment.Bothering Caleb.At best, Caleb puts his book down and pays attention to him, and at worst Caleb scowls at him over his book and Molly knows he’ll pay for it later in some delightfully inventive fashion; either way, he wins.





	Lesson Learned

**Author's Note:**

> Well then.
> 
> I certainly hadn't expected to write explicit widomauk smut, but here we are.
> 
> I'd like to thank the CR discords I'm in for their encouragement and inspiration. You guys are amazing :)
> 
> This is assumed to take place in the future, when Caleb is high enough level to be casting Magnificent Mansion, and is in a _much_ healthier headspace than I usually write him in.

It’s been a good day.

They’ve made fair time traveling, but since they’re not on a deadline, there’s no pressure to push, and there’s definitely a difference to traveling at a leisurely pace versus traveling when you know there’s somewhere you need to be. Everyone’s in a good mood, joking and teasing, and dinner’s a cheerful affair in Caleb’s Mansion. Relaxed, at ease-

Except for Molly.

He can feel Caleb’s gaze on him from across the table, eyes gently narrowed and wearing a barely-there smug smile that makes something twist deliciously in Molly’s gut.

Their travel earlier was calm and relaxed, but Molly gets bored easily, and there’s only so many ways he can practice his cards, or clean his swords, or doze in the sun in the back of the wagon with Frumpkin, and so he’d turned to his next favorite form of entertainment.

Bothering Caleb.

At best, Caleb puts his book down and pays attention to him, and at worst Caleb scowls at him over his book and Molly knows he’ll pay for it later in some delightfully inventive fashion; either way, he wins. Today, it turns out it’s the latter outcome.

After dinner everyone disperses to their rooms for the night, and Molly follows Caleb up to the room Caleb’s created for the both of them, tail swaying behind him with anticipation. He knows Caleb’s planning something, he just doesn’t know _what_. Whatever it is, though, he’s certain he’ll like it. Despite Caleb’s originally reserved nature, Molly’s had the utter delight of discovering the application of Caleb’s perfect memory combined with the sheer amount and variety of smut he’s read. Caleb is creative and innovative, and Molly always enjoys his ‘punishments’. He expects this time will be no different.

Molly opens the door to their room and waves Caleb through, following in behind him and shutting the door with a quiet click. Molly’s just turning to face Caleb when a hand lands on his shoulder and shoves him back against the door, Molly's breath going out of him in a quiet _oof_. Caleb pushes into his space and Molly’s pulse quickens at the proximity.

“Well hello there. Was there something you wanted?”

Caleb’s eyes narrow, and again there’s that hint of a smile. It’s a smile that says Caleb’s mind has been hard at work thinking up something spectacular. “ _Ja,_ I would like to have a word with you about you pestering me earlier, Mr. Mollymauk. I was trying to read and you were very-” Caleb leans in and flicks his tongue against Molly’s lips, “ _-very-_ ” kisses him, searingly hot before pulling back, nipping Molly’s lower lip,“-distracting.”

Molly hums, feeling heat start to suffuse him and making his tail curl in twists against the door. He licks his lips and raises a brow at Caleb and does his best look innocent as he can manage while his lips keep pulling up to a grin. “Was I? Oh, well, isn’t that terrible.”

“Mmhmm. I think perhaps I should teach you a lesson about distraction.” Caleb’s voice has gone deeper, his accent dripping from his words like honey, and Molly shivers as a thrill goes down his spine and to the tip of his tail. He swallows, mouth suddenly dry. “Well, Mr. Caleb, if you feel you must, I am as always ready to be an apt pupil for you.”

Caleb’s smile pulls wider. “I was hoping you would say that.” He takes a step back and Molly sways toward him, but Caleb stops him with a hand on his chest, his smile softening when he meets Molly’s gaze. “Go take a bath, _schatz_. Be thorough, and I will be waiting for you when you are done.”

Molly follows Caleb’s directions, taking as quick a bath as he can while still getting clean. He wanders out into the bedroom a little while later, pleasantly warm from the bath, skin still gently flushed from the heat of the water and the vigor with which he dried himself off. He doesn’t bother with clothes, figuring he’ll just have to take them off again in a moment, and saunters toward where Caleb is seated in a comfortable chair by the fireplace; he’s removed his boots, and his books and harness are resting neatly on top of his coat on the dresser. Caleb’s got his shirt untucked and the sleeves rolled up to his elbows, bare feet propped up on a stool as he reads. Molly takes a moment to appreciate the view; Caleb really is quite striking, especially backlit by the soft firelight.

Molly clears his throat and strikes a pose, hip cocked and tail languidly swishing behind him.

“Your incredibly attractive student has arrived for his lesson, Professor Widogast.”

Caleb’s lips barely twitch, but he sits up, putting his book aside as he sets his feet on the floor and looks Molly over. Molly’s skin heats under the scrutiny, and he could swear he can feel the weight of Caleb’s gaze as it rakes over him. Caleb stands and fairly prowls his way across the room to Molly, and oh, it’s going to be one of _those_ evenings.

Caleb stops a few feet away, and Molly wants to reach for him, but that’s not how this game goes, so he waits, only his tail belying the nervous anticipation running through him as it lashes from side to side. Caleb meets his gaze, and it’s heated, excited, and something unfurls in Molly’s chest at the knowledge that Caleb’s going to enjoy this just as much as he is.

“Go lay on the bed, Molly, on your back, and relax.”

Caleb’s words are quiet, but no less expecting to be obeyed for it, and Molly scrambles toward the bed now that he has his orders. He has a passing moment to notice the bed doesn’t look the same as normal- the headboard and footboard more ornate than Caleb usually bothers with for their room, carved with the design of twisting vines that spread to twist up the posts of the bed- before he’s hopped up into the middle of the mattress and flopped on his back. He lets out a pleased sigh; this bed is one of his favorite parts of the whole Mansion.

“Are you quite comfortable, _schatz_?” Caleb’s tone is bemused, and Molly lifts his head to smile at him where he stands at the foot of the bed.

“Quite, darling. I love this bed almost as much as I love you.”

Caleb smiles at him, fond. “I am glad to hear that, _schatz_.” Caleb then speaks a word in a language Molly doesn’t know and the vines carved into the head and footboards of the bed come to life, slithering down across the mattress faster than Molly can follow and winding around his wrists and ankles; they pull his limbs gently but firmly until he’s spread out on the bed like a starfish. Molly has a moment of stunned amazement, and when the vines stop moving he gives an experimental tug at his wrists. The vines still look as if they’re made of wood, easily holding him in place, but they’re soft, comfortable, and he’s unlikely to hurt himself even if he thrashes.

“And how about now, are you still comfortable?”

“Why, Mr. _Caleb_ , you’ve been holding out on me.”

There’s a quiet chuckle and then the soft pad of footsteps as Caleb moves to the side table. Molly turns his head to look, and sees Caleb picking up a glass vial and a small bowl, setting them next to Molly’s hip before he climbs up on the bed himself. Caleb runs a warm hand up Molly’s thigh, sweeping his thumb back and forth over the dip of Molly’s hip, and Molly hums, relaxing further into the bed. Caleb pulls his hand back after a minute, and Molly pouts, earning him a huff of laughter.

“Do not give me that look, you are here to learn a lesson, _ja_?” Caleb’s voice darkens ever-so-slightly, and Molly shivers pleasantly.

“ _Ja_ , Professor.”

The look Caleb gives him would be withering if Molly didn’t know him well enough to see the flare of amusement behind it.

“Then let us get started.”

Caleb uncorks the vial and dips a finger into the oil before lowering the slicked fingertip to circle lightly around Molly’s entrance. Molly is quickly writhing and trying to press his hips down enough for Caleb’s finger to slip inside, but Caleb just pulls his finger back, and Molly groans in frustration.

“ _Tease_.”

Caleb laughs and resumes circling another moment before finally pressing the finger in. Molly sighs, wiggling his hips as much as he can, trying to get Caleb to go deeper, but Caleb won’t be rushed.

“Patience, _schatz_.”

“Fuck patience, just... _please_.”

Caleb arches an eyebrow at him, then smiles, and the smile looks a combination of smug and sinister that has no business looking as attractive as it does.

“As you wish, _liebling_.”

He’s still careful as he works Molly open, but he’s no longer holding off, no longer drawing things out, and soon Molly’s gone from mostly hard to fully hard, squirming on Caleb’s fingers. Caleb gives one last pointed twist of his wrist, just managing to catch the edge of Molly’s prostate, and Molly keens, hips jerking up before Caleb pulls his hand back and wipes it on the coverlet. He pats Molly’s thigh.

“And now for the fun part.”

“Wha-” Molly’s gasping for air, lost in a haze of arousal, but he tries to focus, because this seems important. “We weren’t already at the fun part?”

Caleb reaches for the bowl that’s been sitting on the bed and pulls something out of it. It’s wet, pale and glistening, and doesn’t look much bigger than Caleb’s thumb, though it’s longer and has a knob on one end. After a second, Molly picks up the scent of ginger, and his brow furrows in confusion.

“I don’t...I don’t understand.”

“You know, Mollymauk,” Caleb holds the ginger up, inspecting it, “There are many interesting things you can learn when you read, and the genre of smut is no different.”

Molly eyes the piece of peeled ginger warily. “Is that so?”

“Mmhmm. Ginger as you know is useful for a great many things- it’s good at seasoning food, it’s good for digestion, helps stomach aches-”

Molly’s confusion only grows. “...okay?”

Caleb turns his head and pins Molly with a look. “And if inserted into certain orifices, it can create rather strong sensations. I hear it’s very intense.”

Molly’s eyes widen in understanding, and he’s not ashamed of the small whimper that makes it past his lips.

Caleb holds his gaze a moment longer, using his free hand to squeeze Molly’s thigh. “You have your word if you need it, _schatz_?”

Molly gulps but nods, stomach doing a flip as he twists his wrists in the vines. “Yes, Caleb.”

Caleb turns, one hand on Molly’s hip to steady him as he uses the other to insert the finger of ginger into Molly’s hole.

Initially, it just feels cool and wet, a little weird, but not bad. Molly wiggles, but the sensation doesn’t change, and he frowns.

“Is it supposed to be doing something?”

Caleb snorts, and grabs the bowl and vial from the bed before getting up and placing them both back on the nightstand. “Just give it a minute, _schatz_.”

Molly sighs and relaxes back to the bed again, his arousal banked slightly at the seeming pause in the proceedings, the tip of his tail flicking gently against the sheets. He’s opening his mouth to tell Caleb that whatever he was trying to do doesn’t seem to be working when he feels... _something_.

It starts as a gentle tingle, like when he uses Jester’s peppermint oil salve on his lips, but it’s quickly growing stronger, developing into a burn that makes him squirm and gasp.  
“ _Oh._ ”

Caleb returns to his side and reaches between Molly’s legs, tapping lightly at the knobbed end of the ginger plug, and Molly shouts, hips coming up off the bed as he inadvertently clenches around it and the burn intensifies before settling back.

“What the _fuck_.”

“ _Ja_ , about that, one of the many wonderful properties of _Zingiber officinale_ is that while it creates a very intense burning sensation, it doesn’t do any actual harm. When I take it out again you will be fine. But in the meantime-” Caleb twists the finger of ginger and Molly nearly chokes on his tongue at what feels like a firebolt in his ass.

“ _Fuck_.”

“Oh, I do not think so.” He takes a loose grip of Molly’s dick, squeezing gently and Molly moans, hips shifting as he tries hard not to clench down. “I still have a lesson to impart, _ja_?”

Molly whines, shifting on the bed as Caleb runs a thumb up the underside of Molly’s cock to swipe under the sensitive head.

Caleb works Molly over, and Molly’s in a sweat, feels like he’s burning up from the inside out, and is surprised to realize he’s still hard, is in fact getting surprisingly close to orgasm.

“Caleb-” his voice is breathy, needy, and he hopes it conveys even a fraction of what he wants. “Caleb, love, _cariad_ _, please_ , please I need-”

“Oh, I’m sure you think you do. But if I just gave you what you wanted, how would you learn?”

Molly growls in frustration when Caleb pulls his hand away. “Caleb, I'm- I'm sorry that I distracted you, I _am_ , just-” he takes a wild swipe at Caleb with his tail, trying to catch his wrist and pull his hand back, but he's- for lack of a better word- _distracted_ , and Caleb catches it easily, pulling it to his lips so he can plant a kiss to the spaded tip as he rubs a thumb just under where the spade connects to the rest of the tail.

Molly tenses up all over, which does _nothing_ good for the state of his hind-end, and a small squeak makes it past his lips. Caleb looks at him, lips still pressed lightly against Molly’s tail, and when he speaks Molly can feel the warmth of his breath and the buzz of his words which _isn’t helping_.

“Are you alright, _schatz_?”

“ _Yes_.” His voice is strained, pulled taut, and Caleb gives a considering hum before swiping his thumb more firmly just below the spade of Molly’s tail; Molly keens, back arching as he pulls at the vines holding him in place, falling back to the mattress with a deep groan when he gets absolutely nowhere. He’s panting for breath, feels like he’s going to combust any moment, and there’s Caleb, smiling gently, serenely even, only the high flush on his cheeks and the thin slivers of blue around blown pupils giving away how affected he is.

Caleb’s expression shifts, turns calculating, and Molly has a moment to think, ‘ _oh fuck_ ’ before Caleb’s sucking the tip of Molly’s tail into his mouth.

The wet heat is blinding, and the sensation zings through Molly like a lightning bolt; his cock twitches against his stomach, and he sobs, hands grasping for the vines if only for something to hold onto. He’s grateful for the anchor as Caleb starts tracing his very talented tongue around the spade’s edges, catching one of the golden rings that decorates it between his teeth and pulling  _very_ gently.

There are noises coming out of Molly he barely recognizes, doesn’t think he’s ever made before, but it’s difficult to focus on much of anything with Caleb working his tail with his tongue and hands, and the blazing stinging heat of the ginger in his ass. Caleb pulls off Molly’s tail with a flick of his tongue that makes Molly twitch, and licks his lips, smiling.

“These are very interesting reactions you are having, Mollymauk. How do you feel?”

It’s not really a word, per se, that comes out of Molly’s mouth, more a confused jumble of consonant and vowel sounds, his brain otherwise occupied by the way Caleb is casually taking him apart and leaving him a mindless pile of quivering jelly on the bed.

“Good, _ja_?” Caleb nibbles at Molly’s tail again and Molly writhes and gasps, the sensation shooting straight to his cock, and maybe he’d crossed a line earlier after all, because he’s sure now Caleb is trying to kill him.

“ _Liebling_.” Caleb’s looking down at him, curious. “Do you think you could come just from this?”

Molly does his best to evaluate, and finds he’s close, so very _very_ infuriatingly close, his cock heavy and dripping on his stomach, flushed a dark plum, and Caleb’s hardly even looked at it, let alone _touched_ it. The burn of the ginger might be waning, or maybe he’s just getting used to it, but it still stings, but in an oddly pleasant way. He’s intensely aware of Caleb’s hand on his tail, thumb once again sweeping back and forth in a maddeningly light arc. He’s come untouched before, so he knows it’s at least theoretically possible, but that had been with Caleb inside him, the stimulation to his prostate pushing him over the edge. He doubts he’ll have that courtesy this time.

“M-maybe?”

“Hmm. Interesting.”

“ _Interesting_? Caleb, you’re killing me, here, _please_ , I need to come-”

“No, you do not. You _want_ to, which is very different.”

Molly does in fact want to come, very badly, and he doesn’t know how to explain to Caleb that if he doesn’t get to come soon he’s going to burn up to a cinder out of sheer frustration, and _then_ where will Caleb be?

“But, _schatz_ , because I love you, I am going to let you.”

Molly wants to cry with relief, his hips tilting up in an attempt to get Caleb to touch him, and Caleb laughs, low and quiet.

“However.”

 _Fuck_. He should have known there’d be a catch.

Caleb rubs his cheek against the spade of Molly’s tail, his scruff scratching pleasantly along the sensitive skin, and Molly shivers.

“I am going to give you a choice, Mollymauk. If you like, I can take the ginger out, and we will see if I can make you come with just my mouth and hands on your tail; an experiment, if you like. If you choose to leave the ginger in, you’ll get my hand and mouth on your tail, but also on your cock as well.”

Molly thumps his head back against the pillows with a huff, pulling at the vines in his hands. He wants the ginger out, the burn to stop, but he also thinks he might die if he doesn’t get Caleb’s hand on his cock in the very near future. What finally sways him is that, as much as he wants the ginger out, he knows that while he _can_ come untouched, there’s no guarantee, and if there’s nothing in him?- better to choose the option more guaranteed to get him off and get him off _well_.

“Fuck, just...leave the damnable root in, just _please_ touch me.”

“But _liebling_ , I _am_ touching you.”

Caleb laughs at Molly’s pained expression and soothes him with a pat to his thigh and a kiss to the tip of his tail. “Alright. Let’s get you seen to, _ja_?”

“ _Finally_ -” Molly breathes, and moans as Caleb winks at him, taking Molly’s tail back into his mouth.

It feels so _good_ , the sensations traveling down Molly’s tail and up his spine; Caleb hums, and Molly jerks in place, crying out before he starts to beg.

“ _Caleb_ , love, _please_ , you said you’d touch me, please make me come, _please-_ ”

Caleb takes pity on him, switching Molly’s tail to his left hand, running the fingers of his right through the pre-cum that’s been pooling on Molly’s stomach. Fingers slicked, Caleb grips Molly’s cock at the base and strokes up, twisting his wrist at the top and drawing a stuttering moan from Molly before dropping his hand back down and starting over.

Very quickly Molly is right on the edge again; between the wet heat of Caleb’s mouth on his tail, Caleb’s calloused fingers on his cock and the waning burn of the ginger every time he clenches, he feels a hair’s breadth from coming. The heat is pooling in his gut, molten and bright, and it’s right there, waiting for him, if he could only just _get_ there.

“ _Caleb_ -” his name leaves Molly’s lips on a moan. “I’m so close, please, I need- I need-”

Taking Molly’s tail from his mouth, Caleb pumps Molly’s cock faster, a little rougher, just this side of too much.

“Come for me, _liebling._ ”

A few more strokes it all it takes before Molly is arching off the bed and fighting the hold the vines have on him as he comes with a wail. Caleb works him through it, murmuring endearments the whole time. Molly eventually collapses back to the bed, twitching, a dopey grin blooming across his face. “Holy _shit_.” It comes out on half a laugh, and he’s not sure he’s ever felt so good in his life.

Caleb lets go of Molly’s cock, and sets Molly’s tail gently on the mattress before quickly getting the front of his trousers open and taking himself in hand. His hand is already slick from Molly’s spend, and it doesn’t take long at all to bring himself off with a grunt, painting Molly’s hip and stomach. Molly’s a bigger mess than he was before his bath, but he really doesn’t care. He feels like he’s melted, and really hopes Caleb doesn’t expect him to move or form coherent thought anytime soon.

He doesn’t realize he’s started to drift until there’s a hand carefully pulling the ginger root out. Caleb murmurs the word from earlier and the vines that have been holding Molly captive unwind and retract back into their respective boards, leaving him sprawled haphazardly on the mattress.

“ _Schatz_.” Caleb’s voice is warm and low, coming from right nearby; when Molly opens his eyes it’s to see Caleb’s stripped down and standing next to the bed. “Are you alright? Feeling okay?”

Molly hums and stretches before falling limply back down. “Feel great.”

Caleb smiles warmly at him and crawls part way onto the bed, holding a hand out toward him. “We should go get cleaned up, _liebling_. The servants will change the bedding for us while we’re gone.”

It takes some coaxing and an offer to wash Molly’s hair for him, but Caleb eventually gets Molly back out of the bed and to the bath. Molly feels amazing, loose and light and dreamy, and he doesn’t even try to stop the delighted purr that rumbles up from his chest as Caleb washes his hair for him and gently rubs a sudsed-up washcloth all over. The burn from the ginger is largely gone now, just as Caleb had said, and he knows by morning he probably won’t feel it at all.

It takes effort to get out of the warmth of the bath, but Caleb promises that soon they can lay down, and Molly soldiers on. The towels are soft, fluffy, and _warm_ as Caleb helps him dry off, following the path of the towel with his lips, leaving kisses in his wake. By the time they return to the bed it’s been cleaned up and remade, the sheets fresh and smelling lightly of lavender. Caleb pulls the coverlet back and urges Molly forward, though honestly it doesn’t take much convincing. Molly nestles into the mattress, enjoying the feel of the sheets on his skin, the softness of the pillows, and then Caleb is climbing in on the other side and pulling him close. Molly goes readily, snuggling in and loosely winding his tail around Caleb’s ankle and Caleb huffs a laugh as he pulls the blankets up over them. In the dimming light of their room, Caleb leans in and presses a kiss to the top of Molly’s head. “ _Liebe dich, Liebes Herz._ ”

Molly’s quickly fading, but manages to murmur, ‘ _I_ _s breá leat, baile croí_.’ before he’s pulled down into the warm arms of sleep.

**Author's Note:**

> (These translations are largely the work of Professor Google, so if you're a native speaker, please feel free to politely correct me!)
> 
>  _liebling_ \- darling  
>  _schatz_ \- sweetheart  
>  _cariad_ \- sweetheart  
>  _Liebe dich, Liebes Herz_ \- "Love you, dear heart."  
>  _Is breá leat, baile croí_ \- "Love you, heart home." (directly inspired by the wonderful [The_Disaster_Tiefling](https://archiveofourown.org/users/The_Disaster_Tiefling/pseuds/The_Disaster_Tiefling))


End file.
